Rhiana Gademsky and Anant Agarwal Of Aidora: How We Leveraged AI To Take Our Company To The Next Level
An Interview With Chad Silverstein
…AI Powered Leave Plan Generator: We’ve built a free, open-to-all AI-powered leave plan generator that helps employees across the U.S. understand their benefits. Navigating leave laws is complex, and this tool makes it significantly easier. It’s even being adopted by other platforms in the leave ecosystem, who link to it directly to add value for their users…
In the ever-evolving and never-ending landscape of business, staying ahead of the curve is a prerequisite for success. Artificial Intelligence (AI) has gone from being a futuristic concept to a daily business tool that executives can’t ignore. In this interview series, we would like to talk with business leaders who’ve successfully integrated A.I. into their operations, transforming their companies in the process. I had the pleasure of interviewing Rhiana Gademsky and Anant Agarwal.
Rhiana is the CEO and Co-Founder of Aidora, an AI-powered leave management platform transforming how HR teams manage employee leave. Before founding Aidora, she held roles in early-stage startups, growth investing, and investment banking, building a diverse background in business strategy and innovation.
Anant is the Co-Founder & CTO of Aidora, an AI-powered platform reshaping how modern companies manage employee leave. He’s spent his career solving complex problems across industries — from leading AI-driven personalization efforts at Google to serving as a Vice President and strategist at Goldman Sachs, where he built financial infrastructure that powered structured product distribution at scale. Known for his ability to go deep fast, Anant blends technical depth with business strategy and execution, and has a track record of building high-performing teams, shaping product culture, and scaling with speed and clarity.
Thank you so much for doing this with us! To set the stage, tell us briefly about your childhood and background.
Rhiana — I grew up as the daughter of engineers, so math and science were always a big part of my life. From an early age, I was drawn to computers — learning HTML to build websites and creating PowerPoint presentations to convince my parents to buy me a MacBook. I’ve always been motivated to tackle new challenges. Whether it was running for student government as a shy teenager, learning to play soccer right before high school and making the team, or being a four-year varsity swimmer, I thrived on pushing myself to take on tough situations. Doing hard things has always excited me and shaped how I approach both personal and professional challenges.
Anant — I grew up in a middle-class family in India where money was always tight, and watching my parents juggle loans shaped me early on. My dad was a serial entrepreneur — he tried everything from running a gift shop to manufacturing plastic goods. Most ventures didn’t work out, but through them, I got a front-row seat to how businesses run, how customers think, and what real hustle looks like. That rubbed off on me. As a kid, I started a neighborhood library funded by small membership fees. I was hooked — not just on building something, but on the idea that if you’re scrappy and thoughtful, you can make things happen. Around the same time, I got obsessed with math. I dove deep, competed at national and international levels, and even filed patents in high school. Math gave me structure; entrepreneurship gave me fuel. That mix still drives me today. I’ve always been pushing to become better — partly to ensure my family never has to feel that financial instability again. At Aidora, I channel that same mindset: solve real problems with precision and heart, and build tools that actually make life easier for people who need it the most.
What were the early challenges you faced in your career, and how did they shape your approach to leadership?
Rhiana — I started my career in finance, a highly hierarchical environment where long hours were valued over original thinking, and leadership often lacked empathy. While I had some great mentors, I saw how this approach left people feeling burned out and undervalued. That experience shaped my leadership philosophy — I learned that being a strong leader means empowering your team to take ownership, work smarter (not harder), and feel supported as whole individuals. At Aidora, I focus on building a culture where people are encouraged to balance their professional and personal lives — building a company is inherently a marathon not a sprint.
Anant — I began my career at Goldman Sachs as a strategist — a role that sat at the intersection of tech and business. I came in straight from college with a computer science degree and virtually no background in finance. Suddenly I was in rooms where everyone spoke markets fluently, and time was the scarcest resource. There wasn’t much room for handholding — so I had to ramp up fast, teach myself the fundamentals, and find ways to contribute without slowing others down. That experience shaped a core belief I carry as a leader: the fastest teams aren’t built on pressure — they’re built on shared context. At Aidora, I make it a point to always create space for questions. I also design each person’s onboarding plan thoughtfully, even in a remote setting, so they can ramp up fast and contribute with confidence. I learned that the hard way — and now I build the environment I wish I had.
We often learn the most from our mistakes. Can you share one mistake that turned out to be one of the most valuable lessons you’ve learned?
Rhiana — In high school, I once got in a lot of trouble for hanging out with the wrong crowd, which led to some tough consequences like being suspended from sports teams and kicked out of clubs right ahead of applying to colleges. It was a wake-up call that no matter how smart or driven you are, you’re also shaped by the people you choose to surround yourself with. Since then, I’ve been intentional about building a circle of people who challenge and inspire me to be better in every way, both professionally and personally.
Anant — One of the valuable mistakes I made was becoming an incredibly strong solo contributor — and staying that way for too long. At Goldman, I thrived in a high-ownership environment. I rose quickly by taking on tough problems end-to-end. But that strength became a weakness. I defaulted to doing everything myself, and as my role grew, I started to see the limits — my impact was tied directly to the hours I could put in. Over time, I realized that if I wanted to truly scale, I had to shift from doing to enabling. That meant sharing the problem space early, investing in others, and building a team that could operate with full context and autonomy. At Aidora, that lesson shows up in how we work. We move fast because ownership is distributed, clarity comes early, and people are trusted to lead — not just execute.
A.I. is a big leap for many businesses. When and what first sparked your interest in incorporating it into your operations?
Rhiana — Leave management has traditionally been handled manually or through service-based solutions, relying heavily on human involvement. When we started building Aidora, ChatGPT had just launched, and as it evolved, we quickly saw the potential to use AI to rethink the entire approach. Instead of replicating the human-driven model, we envisioned a virtual leave case manager that combines the best of human support — empathy, guidance, and accuracy — with the consistency, scalability, and cost-effectiveness that only AI can offer.
Anant — I’ve been working with AI for over a decade — from personalization to real-time decision systems at scale. So when we started Aidora, AI wasn’t an add-on — it was the foundation. Leave management is packed with nuance, regulation, and edge cases. I saw an opportunity to give every employee access to the kind of guidance you’d expect from an expert — instantly, 24/7, and without needing a huge support team. When LLMs started to break through, it became clear the barrier to building with AI had collapsed. What once took months could now be prototyped in days. That shift unlocked a new level of ambition — not just for our product, but for how we operate. Today, we use AI across the board — from rolling out accessible features to powering internal operations — all designed to make Aidora a lot faster and smarter at scale.
AI can be a game-changer for individuals and their responsibilities. Can you share how you personally use AI and what are your go-to resources or tools?
Rhiana — Honestly, I don’t know how I’d run this company without ChatGPT. It’s become an essential tool for drafting emails, blog posts, newsletters, and more. Beyond content creation, I use it as a thought partner when brainstorming partnership agreements or navigating new challenges. It’s been an incredible efficiency booster and a force multiplier, freeing up time and brain power to allow me to focus more on strategic thinking and decision-making.
Anant — AI is my primary brainstorming partner — and one I rely on across roles. I’ve built custom GPTs that act as my Chief Information Security Officer, helping navigate security questionnaires and audits, and another that helps me explore messaging and positioning angles for PR and comms. For product discovery and understanding edge cases, I often use ChatGPT, Gemini, and Claude to explore nuanced user scenarios or pressure-test assumptions. These tools let me move faster, cover more surface area, and get to sharper answers without the usual friction. And obviously, I also use Cursor — to shorten build cycles, ship fast, and accelerate momentum across the stack. It’s not about replacing expertise — it’s about reaching it sooner, and scaling my thinking across all the hats I wear as a founder.
On the flip side, what challenges or setbacks have you encountered while implementing A.I. into your company?
Rhiana — One of the biggest challenges is that as more people use ChatGPT, content — especially sales emails and marketing copy — has started to sound generic and uniform. I’ve noticed that it’s easy to fall into the trap of using AI-generated text without personalizing it. To combat this, I push my team to treat AI-generated content as a starting point rather than the final product. We focus on editing and refining it to make sure it sounds authentic and aligns with our unique voice. Since AI is a tool everyone has access to, the key is being creative in how you cut through the noise of endless AI-generated content.
Anant — Implementing AI inside a company is exciting — but making it work reliably, every day, is a whole different challenge. Tools like ChatGPT, and even the custom GPTs I’ve built for security and PR workflows, don’t retain context across sessions. Every interaction starts from scratch — there’s no continuity. To keep them effective, we’ve had to build thoughtful scaffolding around how they’re used. The same goes for tools like Cursor. It can dramatically speed up development — but only if the context is set up well. Without that, performance can swing: one day it’s spot-on, the next it misses the mark. AI is magical — but to consistently derive value from it, you have to build thoughtfully around its edges and make sure it’s always operating within the right context.
Can you share the top 5 A.I. tools or different ways you’re integrating AI into your business? What specific functions do they serve and what kind of result have you seen so far?
Rhiana & Anant (we’re combining this):
1 . AI Powered Leave Plan Generator: We’ve built a free, open-to-all AI-powered leave plan generator that helps employees across the U.S. understand their benefits. Navigating leave laws is complex, and this tool makes it significantly easier. It’s even being adopted by other platforms in the leave ecosystem, who link to it directly to add value for their users.
2 . Custom GPTs: As Anant mentioned, we’ve built custom GPTs for specific use cases — one example is answering security questionnaires. While we follow state-of-the-art security practices, responding to vendor assessments is time-consuming. Our custom GPT reads our documentation and drafts a first pass, saving hours of manual work.
3 . ChatGPT / Gemini / Claude:
Rhiana leverages these tools for content creation — drafting emails, newsletters, and blog posts. Anant uses them for product discovery, identifying edge cases, and pressure-testing assumptions. Beyond specific tasks, we also use them as daily brainstorming partners. Being a founder means facing new challenges constantly, and these tools give us quick feedback and ideation support.
4 . AI NoteTaking: We use AI notetaking to scale knowledge across the team — capturing conversations, summarizing key points, and helping everyone operate from shared context. This has been especially useful in onboarding and cross-functional collaboration, allowing team members to ramp faster and execute with alignment.
5 . Cursor for Engineering Velocity: AI-assisted coding is the norm at Aidora. Cursor has helped our team ship faster, fill knowledge gaps across different parts of the codebase, and maintain high momentum without compromising on quality.
There’s concern about A.I. taking over jobs. How do you balance A.I. tools with your human workforce and have you already replaced any positions using technology?
Rhiana — We haven’t replaced any positions with AI, but it has allowed us to run leaner, particularly in sales, marketing, and operations. By supplementing knowledge gaps and handling some executional tasks with AI tools, we can operate efficiently without needing to hire for support roles. That said, there’s no replacement for the human touch in areas like relationship-building and sales. AI enhances our team’s productivity, but it doesn’t replace the creativity, empathy, and nuance that come from human interactions.
Anant — Like Rhiana mentioned, we haven’t replaced any positions with AI — but it’s absolutely allowed us to run leaner. On the product, engineering, and support side, AI lets us punch above our weight. One engineer can ship more, support can scale with fewer handoffs, and we can prototype and test faster without needing a large team. That said, AI is a force multiplier — not a replacement for thoughtful product sense or deep technical judgment. We still rely heavily on people to make the hard calls, shape the experience, and maintain the quality bar. AI helps us go faster, but the human layer is what makes it all hold together.
Looking ahead, what’s on the horizon in the world of AI that people should know about? What do you see happening in the next 3–5 years? I would love to hear your best prediction.
Rhiana — AI is advancing faster than most people expected, and we’re already seeing the potential of agentic AI — systems that can make autonomous decisions. As these capabilities grow, I believe we’ll see billion-dollar companies built by teams of just 10 people. AI will handle much of the operational, customer support, and even strategic work, allowing small teams to scale faster and more efficiently than ever. It’s going to completely change how startups are built and what it means to grow a business.
Anant — I think we’re heading toward a world where every individual works alongside a team of AI collaborators — not tools, but active participants that can carry out complex tasks, take feedback, and improve over time. You’ll be able to onboard an AI specialist just like you would a teammate: give them context, assign a task, review their output, and iterate. The workflow will look more like managing a high-functioning team — except that team is entirely digital. We’re already seeing glimpses of this, but over the next few years, the shift will be profound. One person will be able to drive the output of an entire cross-functional team — engineering, design, analysis, strategy — just by collaborating with well-trained, specialized AI systems. That kind of leverage will fundamentally change what individuals are capable of, and how we think about productivity, scale, and ownership.
If you had to pick just one AI tool that you feel is essential, one that you haven’t mentioned yet, which would it be and why?
Rhiana — One AI tool I find essential but haven’t mentioned yet is Fathom Notetaker. It’s a game-changer for capturing and summarizing meetings. Instead of scrambling to take notes during important calls, Fathom automatically records and transcribes conversations, highlights key points, and even creates follow-up tasks that are pushed directly to our CRM. This allows me to stay present and engaged while knowing I’ll have an accurate record and actionable next steps afterward. It’s especially valuable for sales calls and internal strategy meetings, keeping us organized and efficient.
Anant — One tool I’ve been using is SuperWhisper — an AI-powered dictation tool that turns my speech into clean, structured text. It’s become essential for the way I review work across the team. As a remote-first company, written feedback is how we transfer context and scale clarity — and Super Whisper lets me go deep without slowing down. Instead of typing out detailed reviews or jumping on yet another call, I can now speak my thoughts, layer in business context, and share nuanced feedback in one go. That’s made the feedback loop faster, more thoughtful, and way more scalable. The team gets to learn from the “why” behind decisions — not just the surface-level comments.
For the uninitiated, what advice would you give someone looking to integrate AI into their business and doesn’t know where to start?
Rhiana — Start small and focus on practical use cases. Look for one or two pain points where AI can make an immediate impact — like automating customer support or data analysis. Tools like ChatGPT or AI notetakers are great entry points because they’re easy to use and deliver quick wins. Don’t be afraid to experiment and stay curious. Sometimes internal uses will inspire external applications — like how we started using AI for internal workflows at Aidora before realizing how it could enhance client-facing processes. Treat AI as a collaborator, not a replacement, and encourage your team to learn and adapt as they go.
Anant — If you’re looking to integrate AI into your business, start by asking: what’s the most inefficient part of your workflow? Or even simpler: where is most of your time getting wasted during the day? That’s usually where AI can create the most leverage — whether by speeding things up, reducing repetition, or creating clarity. Another great entry point is to look at areas where you lack deep expertise. That’s where AI really shines. Pair yourself with an AI model and prompt it to act as the best version of what you need — a world-class PR strategist, a top-tier security analyst, a financial planner. Use it to help you navigate the task, and in the process, you’ll both move faster and learn more. The real power of AI isn’t just automation — it’s augmentation. If every member of the team uses it this way, they’ll level up faster, and the whole company becomes insanely efficient and fast-moving.
Where can our readers follow you to learn more about leveraging A.I. in the business world?
Rhiana — You can follow me on LinkedIn (both my personal page and Aidora’s company page) for insights on leveraging AI in business. We also share valuable content on our company blog, where we discuss how AI is shaping the future of leave management and HR operations.
Anant — In addition to the company page and blog that Rhiana mentioned, I also regularly share how we’re using AI at Aidora — whether it’s building faster, scaling smarter, thinking through user journeys, or designing more empathetic experiences. You’ll find those updates on my LinkedIn profile, along with deeper takes on product and technical strategy.
This was great. Thanks for taking time for us to learn more about you and your business. We wish you continued success!
About the Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Rhiana Gademsky and Anant Agarwal Of Aidora: How We Leveraged AI To Take Our Company To The Next… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.